Sodium Bicarbonate → (5-pyridin-3-ylfuran-2-yl)methanol

Participants

Reaction Steps

To a slurry of 23 (54 mg, 0.31 mmol) in CH3OH (5 mL) was added sodium borohydride (12 mg, 0.31 mmol) in one portion and the resultant solution was stirred at room temperature for 10 min. The reaction was stopped by the addition of aqueous sodium bicarbonate (50:50 satd. soln./water, v:v) and the CH3OH was removed in vacuo. The residue was partitioned between water (20 mL) and ether (20 mL), the organic layer was collected and the aqueous fraction was re-extracted with ether (2×20 mL). The combined organic portions were washed with water (20 mL), dried (MgSO4), filtered and concentrated in vacuo to afford the title compound 45 (50 mg, 92% yield) as an off white solid: mp=119-120° C.; 1H NMR (CDCl3, 500 MHz) δ 8.88 (s, 1H), 8.42 (m, 1H), 7.88 (m, 1H), 7.27, (m, 1H), 6.65 (d, J=3.1 Hz, 1H), 6.38 (d, J=3.1 Hz, 1H), 4.66 (s, 2H); LRMS (ESI) m/z calcd for C10H10NO2 [M+H]+ 176. found 176; HRMS (ESI) m/z calcd for C10H10NO2[M+H]+ 176.0712. found 176.0694; HPLC>98% (tR=4.60 min, 55 (A):45 (B): 0.032 (C); tR=3.64 min, 55 (A):45 (B): 0.1 (C)).

Provenance & Evidence